I’ve been writing for them since 1990: sports, business, real estate, you name it!

A few thoughts — I have been fulltime freelance, (this time, have done it many times before for years on end), since 2006; I live in the spendy NYC suburbs. I write for a wide range of publications, from The New York Times to Cosmopolitan, Marie Claire, More and websites like Quartz.com and Investopedia. (I also teach freelancing, writing and blogging, privately to individuals.) Samples and rates here.

I won’t talk here about your need to be a great writer or boost your “brand” but the array of other skills you also need to succeed in a highly competitive business.

A few thoughts:

1) If you’re simply not making enough money to meet all your costs, (and save money as well), take on part-time work and make sure you remain solvent by so doing. Babysit, tutor, dogwalk, retail — do whatever it takes to keep your credit score stellar and your bills paid, always, on time.

I took a part-time retail job in Sept. 2007 when the recession hit hard and stayed in it for 2.5 years until I had replaced that income and doubled it (monthly); people (i.e. ego-threatened writers) kept saying to me (since my previous job had been as a NY Daily News reporter)…”Oooooh, I could never do that.” Oh, yes you could. Get over yourself and make the money you need. Your landlord or mortgage company couldn’t care less if their payment money comes from the NYT or from….anything else. And, oh yeah, that grueling, low-status, low-wage job experience became my well-reviewed NF book , “Malled: My Unintentional Career in Retail” and won me a TV option from CBS for a sitcom.

2) See point one — you never know what will happen if you dare to step off the well-trodden and safe/comfy path of: “I’m a freelance writer.” Detach your ego and status anxiety from your income, always. Yes, of course, be excellent, but do whatever work you take on to the best of your ability. Excellence shows and people appreciate that.

3) Do everything you can to separate yourself from the pack. There are thousands of us; one “secret” women’s writing group I belong to online has — (yes, really) — almost 2,000 people who self-identify as freelance writers. So figure out what you do better than anyone or more quickly or more efficiently (not more cheaply!) and seek out clients who really value those skills and will pay you well for them.

I speak two fluent foreign languages, have published my photos in major media, and have no kids or pets and have been to 39 countries, often alone — so I can travel easily and work in other languages. Many people can’t or have never done so. That wins me good work.

4) Be a human being. When possible, get to know your clients/editors as people — they, too, have pets and kids and birthdays and illnesses and surgeries. Send them nice cards and/or flowers. Check in with them every few months, and just ask “How’s life for you these days?” I did that for one editor facing very serious illness, someone who had not assigned me work for several years and I wondered if she ever would again. She did. I would have done this anyway. Your clients are just as human as we are; in other words, create and nurture your professional relationships with care and sincere thoughtfulness.

5) Don’t expect (too) much too soon. By which I mean, get a very clear sense of your current and true market value and work from there. Just because you want to be in a Big Name Magazine right now doesn’t mean you’re ready or the editor agrees. Ambition matters, but realism and a little healthy humility also have value, (says this native Canadian.)

6) Be positive, upbeat, friendly and confident. The economy is still shitty and shaky for many people and working with someone smart, capable and who will not let them down — no matter what! — is appealing to clients, some of whom may, realistically, fear losing their jobs if you screw up.

7) Live as low/cheaply as you possibly can. The less overhead you carry, the more creative freedom you have to take on and do interesting work more slowly — i.e. work of serious long-term value, not just buying this week’s groceries.

On assignment this year in rural Nicaragua

8) Reach out for new non-journalism opportunities, every day: online, by phone, through social media, at events. Two of the most life-changing, fun, challenging and well-paid opportunities for me in 2014 came because I simply took a chance and reached out (i.e. cold-called) two major organizations I never thought might welcome my skills. They did and I’ve never been happier as a result. Just because we’re “freelance writers” doesn’t mean we only have to work for really crappy pay from struggling/cheap media companies.

9) If you keep comparing your income to the Big Stars making Big Bucks, you’ll die. Just focus on what you can do, well and consistently. There is always going to be someone making a lot more $$$$ — and crowing loudly and tediously about it. Just do great work!

10) Have fun and take very good care of yourself — go for long walks, alone or with your dog or a good friend. Get plenty of deep sleep, including naps. Go see a movie or spend an afternoon at a gallery or museum. Eat your vegetables! Being a freelance writer can be terrific, but also lonely, isolating and wearying, leading to burnout. This is a sort of job that requires mental, physical and emotional stamina. Rejection is normal. Get over it!

For many people, it’s a cherished dream: work at home, no commute, wear PJs til noon, no crazy boss or office politics!

I’ve been writing for a living for 30+ years, and have been freelancing, this time, since 2006. Here’s what my week this week — typical in some ways, very unusual in a few others — looks like:

Sunday

I normally don’t work on weekends but I’m facing multiple deadlines and have to interview people this afternoon — including boys ages 8 to 11 for a story for Boys’ Life, the magazine of the Boy Scouts, for whom I’ve been happily writing for years. With no kids of my own or nephews, I need some great quotes from these boys, one of whom has a shrieking sibling in the background during our conversation. I email several clients to track down late payments and invoice a few others.

I check in with the Hollywood scriptwriter who’s been writing a pilot script for “Malled” for CBS for months. It’s now, finally, with the network executives who can give it a green light — or not. How weird it might be to have a television character based on…me.

Monday

Eight hours at the hospital getting every bit of my body tested for upcoming hip surgery.

I’m home by 4:00 p.m., worn out from listening carefully to so much complex information. Terms like “blood loss” don’t help my nerves.

I still have to finish up my Boy Scout story; invoice Reuters.com for an op-ed I wrote last week; try to find out the status of two stories I pitched to The New York Times (for whom I’ve been writing since 1990.)

Working freelance means wearing a dozen hats at once: marketing, coming up with ideas, finding editors to buy them (at the right price!), billing, pitching, researching, interviewing, reading, writing, finding sources and — the worst! — chasing down late payments. One client screwed up so badly I still haven’t been paid for a story that ran in November.

So, like every freelancer I know, I hustle for work constantly — and use a line of credit to pay every bill promptly. My bank charges 19 % APR (!) and $12 every time I use the overdraft protection, which these late payments force me into.

I can only afford, finally, to get this surgery because I’ve saved enough to take 4-6 weeks off entirely for my recovery. Freelancers have no paid sick days!

The anesthesiologists’ office warn me that a typical bill for my two-hour operation is $3,800, of which our health insurance will pay, at most, $1,000. I’m in no mood to wake up facing a $2,800 bill. One more thing to try not to worry about.

Tuesday

Into New York City for a haircut. Next week my husband, (a professional photographer and editor), will take my new headshot, which I need for my websites, blog, book events, speaking engagements and other professional gigs. I get asked for it a lot, and everyone who runs their own business should have a good, recent, flattering one.

I’ve tried to clear the decks of work almost completely, so I can go into this major operation without worrying I will disappoint someone or miss a deadline. I still have two paid blog posts left and five days to get them done. I’ve been trying to sell a story about the surgery, but no one has bitten. (Yet!)

Wednesday

I fly to New Orleans, where I’ll attend a cocktail party at a conference of retail business owners. I’m excited but nervous. I hate turbulence and my last flight (home from Chicago in November) was horrible. I enjoy doing public speaking, but writers generally like to have our words speak for us, and giving a great speech isn’t a natural or obvious talent. Last year I hired a terrific speaking coach whose advice and tips made me much more confident.

Thursday

At 1pm eastern time, I join an hour-long conference call of 15 fellow writers all across the U.S. who serve on the board of the American Society of Journalists And Authors, a 1,400-member group that advocates for writers’ rights, improved working conditions and pay. I’ve served on the board for five years and am leaving it in July. I’ve enjoyed it, but I’m pooped. At 3:30, I’m speaking on the topic of how to hire, manage and motivate low-wage employees, something I learned firsthand when I worked for 27 months as an associate at The North Face, an outdoor clothing company, and which formed the basis of my latest book, “Malled: My Unintentional Career in Retail.”

Friday

Play day! New Orleans is one of my favorite cities to visit. I’ve been there twice before, once in the spring of 2002 to interview men and women for my first book, about American women and guns. It makes a city a very different place when you’re there to work and try to get to know even a little of the political and economic structure and whose opinions matter most there.

Just got off the phone with an agent who sells “E and O” — errors and omissions insurance — as I start to figure out how to protect my ass(ets) as a writer. He’s sending me several applications, one of which, the multimedia version, is really long. Of course it is!

The joy of “independent writing”? Anyone can sue us anytime. The latest darling of the suit-happy are SLAPP suits — Strategic Lawsuits Against Public Participation. Which means, unless you work on staff for a Big Media Company (with in-house staff attorneys whose highly-paid job it is to protect you and, more importantly, your employer) you’re toast, baby.

More and more, writers are strong-armed into signing contracts that leave us holding the bag in case someone we cover sues the media outlet for whom we’ve done the — freelance — work.

There’s no better way to make sure we write about puppies and kittens and rainbows than knowing one false move can mean our IRAs are going to get garnisheed in a settlement. The saber-rattling by those with very deep pockets – hmmmm, the wealthy and powerful? — means many of us slap duct tape over our mouths every morning, no matter what madness and malfeasance we discover.

“Independence” is a relative term.

One lawyer I spoke to, knowing the writing life, (beyond lucrative TV and film), delicately inquired, “Do you have any assets?” The answer, having worked long and hard and been really disciplined about driving clapped-out old cars and wearing (mostly) consignment shop shoes is “Yes.” I save 15 percent of my income every year, even when that income is so small I think: “Why bother?”

And, this being the U.S, a nuisance lawsuit is both nauseating and much more probable than I’d like.

Suiting up, then, is quite the challenge, requiring the (paid) services and advice and expertise of my accountant (becoming a company); an attorney (making sure it’s all done properly) and an insurance agent. Unlike car or home insurance, I can’t cough up that dough each month — it’s one lump sum, on my income, a fortune. There is cheaper insurance but — funny thing!– it’s capped at a much lower amount.

Why should you care?

Every day, there are posts I don’t write — or write and don’t publish — because, who needs it? Like many of my colleagues, I’ve got other things to worry about without some $$$$$-mad aggrieved plaintiff ruining my life. That costs you, dear readers, because there’s all sorts of (interesting) stuff it simply isn’t worth mentioning, for fear of such a suit. I know, personally, other independent writers backing away slowly, if regretfully, from smart, incisive, tough, investigative work for this very reason.

Believe it or not, not every writer wants to focus on all-fluff-all the time. But without a safety net, you can’t safely leap too far.

I’m thinking of setting up a Paypal account — you really want my unvarnished opinions? Help me speak truth to power, and not lose my home/assets/savings in the process.

I’m the broad behind Broadside, Caitlin Kelly, a career journalist. photo: Jose R. Lopez You’re one of 13,3430 followers, from Thailand to Toronto, Berlin to Melbourne. A National Magazine Award winner, I’m a former reporter and feature writer at The Globe and Mail, Montreal ... Continue reading →